Tall Order Wrangling a formidable fashion machine like Boss is no easy feat, but with his perfectionist’s focus and superhuman energy, designer Jason Wu is the man for the job. Designer Jason Wu in his own clothing.

Who’s the Boss?

Five years ago, he was the up-and-coming designer behind Michelle Obama’s Inauguration gowns. Now, Jason Wu is being lifted to new heights by fashion behemoth Hugo Boss.

Inside a cavernous warehouse on an industrial stretch of Brooklyn, a model walks back and forth in a man-made wilderness of spindly birch trees. She wears a streamlined red dress and black patent leather boots, her blonde hair in a severe ponytail. Taking slow, deliberate steps, she stops every so often to gaze into the lens of the camera gliding alongside her on a dolly—the intimidating starkness of her pale face and unblinking blue eyes giving way to a trace of mischief that pleases the young male intern watching from a few feet away. “Oooh, very chic!” he says. “We got it.”

Correction: The intern is, in fact, Jason Wu, who is in charge of today’s proceedings, and who at 31 years old remains as slight and baby-faced as he was back in 2009, when Michelle Obama gave his nascent career a storybook gloss by wearing his ivory silk-chiffon Swarovski-crystal-embellished gown to the Inaugural balls. “I’m still very naive-looking, aren’t I?” Wu says with the sly grin of someone who takes pleasure in the contradictions between appearance and reality. “From a visual standpoint, I’m not very convincing, right? I think when I first started here, a lot of people were thinking, Does this kid know what he’s doing?”

Wu is referring to the latest addition to an impressive if unorthodox résumé that includes, but is not limited to, designing doll clothing while in prep school, dropping out of Parsons the New School for Design to launch his own label, dressing the First Lady, and, most recently, becoming the artistic director of Boss, Hugo Boss’s women’s wear line, which is the reason he’s on set this April afternoon. The shoot is part of Wu’s sweeping effort—along with the retooled campaign featuring the English model Edie Campbell; the decision to show Boss for the first time during New York Fashion Week; and, most important, his introduction of more ladylike silhouettes—to make the Boss woman “more relevant, prominent, and visible,” as the company’s CEO, Claus-Dietrich Lahrs, describes Wu’s mandate. After being edited into a continuous loop, the film will be played in Hugo Boss stores around the world when Wu’s fall collection, his first for the company, arrives. “I’ve already changed the clothes,” Wu says. “Now it’s about changing the way people look at them.”

Wu’s eponymous label is associated more with reserved, slyly sexy elegance than avant garde inventiveness; the Boss job provides him with an outlet to remind people that he is a more versatile designer than they may have thought. Since taking over, he has made it his mission to apply the company’s history and expertise in men’s wear to its women’s clothes, taking the core elements that have made Hugo Boss a staple of anonymously dashing financiers (precise, minimalist suiting) and giving them a softer twist (flowing pleated skirts, intricate embroidery). The initial results—praised by Women’s Wear Daily as a “natural fusion of Germanic references and feminine flou”—include an assortment of stern black and muted-gray belted jackets paired with sheer dresses and mannish loafers. “Why pretend this isn’t a men’s wear company first?” Wu says. “The made-to-measure stuff they do for men is out of this world. But they weren’t bringing any of that over to women’s.”

“Making everything look effortless takes a lot of effort.”

There are many designers who would view a shoot like today’s as a nuisance: a corporate chore that distances them from the creative incubator of the studio. Wu is not one of them. Synergy, branding opportunities, marketing strategies—he discusses such matters with the same ambitious zeal as he does, well, just about everything, including the refined tailoring that has made his own line a favorite of women like Diane Kruger, Michelle Williams, and Zoe Saldana. “This is a big company, a machine,” he says of Boss. “What’s been missing is a single, unified message that translates throughout the entire company, all the way down to the stores and customers.” The birch trees on the set, for instance, are meant to echo those that lined the runway of his debut show in February, which in turn were meant to echo the trees at the Hugo Boss headquarters in Germany. It was there—fittingly, for a designer with dreams of turning his own company into a formidable machine—that Wu found inspiration for the fall collection’s “nature meets architecture” theme.

Just yesterday, Wu was in Hong Kong, on a 24-hour trip to celebrate the opening of a Hugo Boss store. He spent the night indulging in three favorite pastimes: networking, posing for photos, and dancing to music provided by Solange Knowles, who deejayed the event. Yet he seems more energized than depleted by a whirlwind schedule that, he says, has him “living out of a suitcase.” A perfectionist eager to put his stamp on every aspect of the company, he has been at the shoot since early morning, efficiently keeping everything moving, courting order the way many designers court chaos. “I’m a very decisive person,” he says at the warehouse in Brooklyn. “Which makes for a very suitable fit with a German company.” It is only toward the end of the shoot that Wu displays the slightest sign of fatigue, leaning back in his director’s chair and closing his eyes for the briefest of moments. “Making everything look effortless,” he remarks, “takes a lot of effort.”

Many in the fashion world were surprised by the pairing of Wu and Hugo Boss. While other designers of his generation compete to out-shock one another, Wu has taken an old-school approach: creating demure, wearable collections that consistently earn solid profits while getting him mentioned as a successor to the likes of Oscar de la Renta and Carolina Herrera. (Though, given his business acumen and love of pop culture—Wu can talk for hours about the most minute details of RuPaul’s Drag Race—a more apt comparison might be Michael Kors.) His signature designs, whimsical and romantic, are a far cry from the austere aesthetic that defines Hugo Boss. “When they first came to me, I thought it was kind of peculiar,” says Wu, now in the back of a town car that’s weaving through rush-hour traffic along Manhattan’s West Side Highway, en route to the studio he had his German employers provide as part of his contract. “I wasn’t very familiar with Hugo Boss, to be honest, and I was only focused on continuing to build my own brand and company.”

In today’s global marketplace, of course, American designers with such aspirations realize them by doing time at storied European fashion houses—a pattern set by Kors (Céline), Marc Jacobs (Louis Vuitton), Tom Ford (Gucci), and, more recently, Alexander Wang, who became the creative director of Balenciaga in 2012 while making it clear he had no intention of sidelining his own label.

That Hugo Boss doesn’t have quite the same sheen as those other European houses was, for Wu, part of what made the opportunity both unique and irresistible. The company has been in the women’s wear business for only 16 years and has never had a prominent artistic director, providing Wu with the resources of a billion-dollar fashion behemoth without the pressure of constantly being held up against the brand’s past designers. “It’s not like I’ve replaced a beloved creative figure,” he notes.

The car comes to a stop on Seventh Avenue, in the Garment District. “This is the think tank, the inspiration zone,” says Wu during the elevator ride up to the Boss studio, which is conveniently located two blocks from his own, allowing Wu “to work my day and night job” simultaneously. Inside the airy, high-ceilinged space dotted with mannequins sheathed in top-secret prototypes, his New York design team, one of many he oversees, has been waiting to show him the progress on the spring collections, which are still in the early stages. Wu spends a productive hour looking at sketches and fabrics—sheer organzas in pale shades of pink, orange, and violet—dismissing those that fail to “continue the message from the first season.” This unwavering efficiency has impressed his new employers. “Jason has been very quick and savvy in figuring out that, in order to take the brand to the next level, we need to expand to a different kind of woman,” says Lahrs, the CEO. “Someone who doesn’t want to just look like a businesswoman.”

When Wu at last heads to a restaurant in the East Village and treats himself to a “slightly dirty” vodka martini, he has been working for 14 hours, which is just the sort of day he prefers. Last year, he and his longtime boyfriend, Gustavo Rangel, who is the CFO of Wu’s company, took a 10-day trip to Hawaii—Wu’s first extended vacation in, essentially, forever. “It was good,” Wu says. “But I don’t think I could do more than 10 days. I got too relaxed. I’m not very good at doing nothing.”

Born in Taipei, Taiwan, Wu moved to Vancouver, British Columbia, when he was 9 (the same year he got his first sewing machine) and was later educated in New England boarding schools. Raised by encouraging parents who run a successful import-export business, he takes an immigrant’s pride in his work ethic and maintains an outsider’s chip on his shoulder, bristling at the idea of anyone thinking his success has come easily or been the result of luck. “Let’s not forget: I work,” he says. “It isn’t like I came on the scene for two days and got appointed by the First Lady. I worked very hard for three years largely unacknowledged, not nearly as hyped as many of my peers. When the opportunity came about, I fought tooth and nail to get it.” Hoping a personal touch would impress Obama, he explains, he delivered the dress himself, with no assurance that she would wear it. “And then, the day after the Inauguration, I rejected at least two superprofitable opportunities—television shows, endorsement deals—in order to focus on turning my brand into serious fashion.”

At midnight, after a fortifying meal and a few glasses of white wine, Wu hails a cab home. He lives, with Rangel and their two cats, in the same modest Midtown one-bedroom he’s been renting since he moved to New York in 1999, at 17. While he has lately become intent on finding an apartment downtown that he can renovate to his specifications, doing so has been a challenge. “When is there time? I’m scheduled down to the minute through…well, let’s see…” He begins tapping the screens of the two iPhones that are always by his side—one his own, the other in a case bearing Hugo Boss’s logo—their calendars synced in color-coded blocks filling every hour, every day, every month. “Basically, through the rest of the year.” He sighs, contentedly. “It’s fine. This place has been very good to me,” he says of his current digs. “I believe in the feng shui of it all—it’s one of the ways I guess I’m really Chinese.” He chuckles. “Besides, I’m still just a young person trying to make it.”

Two weeks later, Wu arrives in Germany for his monthly round of meetings at the Hugo Boss headquarters. Located in Metzingen, a sleepy pastoral town not far from Stuttgart, the campus is a sprawling, state-of-the-art world unto itself: 2,000 employees moving between glass-concrete-and-steel buildings that bring to mind a cross between war bunkers and airplane hangars. “Isn’t this place crazy?” asks Wu as he walks through the atrium of the central building, where a video featuring his fall collection, shot by Inez van Lamsweerde and Vinoodh Matadin, plays on huge LCD screens rising from the floor like stalagmites. Wu first toured the grounds in secret last spring, when he was being courted by his new employer. “They snuck me in through the back door on a weekend, when no one was working,” he recalls. Some of Hugo Boss’s high-end clothes are made on-site, in the so-called technical center, where skilled tailors man machines that churn out hundreds of garments daily. These are then tested in a “climate box” that simulates how the weather conditions in different markets might affect the fabrics. “What I saw was this whole universe that was fully realized but, remarkably, hadn’t been exploited for all it could be,” Wu says. “Whenever I’m here I’m always doing a million things at once,” he continues, describing the lookbooks to be shot, the plans for the spring 2015 show in New York to be budgeted, the never ending succession of meetings about everything from store windows to mannequin displays. The most important gathering this visit is a summit of all the design teams—clothing, accessories, shoes, and knitwear—for the first time since Wu took the helm. They meet on a Tuesday morning, in a sun-drenched conference room near Wu’s office, which he keeps so spotless it could be mistaken as vacant. “Good morgen!” Wu says with a smile, greeting the various teams and, in the process, exhausting the extent of his German. “There are so many of you! How exciting!”

As the meeting gets under way, Wu’s demeanor shifts: The light, jokey disposition is replaced by a more serious, businesslike one. His role requires both a macro and micro outlook—thinking about designs that won’t be in stores for more than a year while tweaking those in the final stages, and making sure the hundreds of people in offices around the world are hewing to his agenda. His New York team, for instance, is here with the edited version of the spring collection he last saw two weeks ago; and the knitwear team, based in Coldrerio, Switzerland, is already playing with concepts for next fall; it is Wu’s hope that having everyone share their ideas today will result in greater cohesiveness. “I want you all to feel very proud of what we’ve already done,” Wu, who prides himself on his ability to corral disparate talent, says at one point. “That said, we can do better. We need to all make sure we are dressing the same woman, all the time.”

And, despite what his job description would have you believe, dressing that woman is, apparently, not Wu’s only concern. Though he has no role in the men’s designs, he has taken it upon himself to oversee the men’s marketing in order to ensure that the two lines no longer feel disjointed. “I mean, it’s not really my title,” says Wu after meeting with the advertising team to go over the fall campaigns. “But it’s needed.”

Throughout the day, Wu is whisked around the campus, changing gears between the creative and business operations without a hitch. He fine-tunes the designs for the handbag collections for the two upcoming seasons. He gives notes on the fall shoe line. During a rare moment of calm, he takes a minute to reflect on the past year. “It’s amazing what we’ve been able to do,” he says. “But it’s still not fast enough for me. I want to do more. It’s been fast, but I always want it to go faster.” He takes a deep breath. “Okay, what’s next?”